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Stable moxifloxacin hydrochloride compound and preparation method thereof

A technology for moxifloxacin hydrochloride and a compound, which is applied to the pharmaceutical field in the field of medicine, can solve the problems of unfavorable industrial production, low yield, complicated operation and the like, and achieves the effects of simplified operation, simple operation and simplified process operation.

Inactive Publication Date: 2014-06-25
TIANJIN HANKANG PHARMA BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its yield is not high and the operation is cumbersome, and it uses poisonous boric acid and anhydride as reaction reagents
CN101830921 uses phenylboronic acid to directly form a chelate with compound 6, although the operation is simplified, but its cost is high, which is not conducive to industrial production

Method used

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  • Stable moxifloxacin hydrochloride compound and preparation method thereof
  • Stable moxifloxacin hydrochloride compound and preparation method thereof
  • Stable moxifloxacin hydrochloride compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] In a 3L three-necked flask, 187g of 3-methoxy-2,4,5-trifluorobenzonitrile, 97.5g of zinc and 1L of tetrahydrofuran were added, 8.6g of p-toluenesulfonic acid was added under stirring, and the mixture was stirred at room temperature for 0.5h. Heat to reflux, and slowly add 217.1 g of ethyl bromoacetate dropwise. React under reflux for 2 hours, cool to room temperature, add 500mL 6M hydrochloric acid and 100mL water successively, stir for 2h, cool to 5°C, a large amount of solids will precipitate out, filter, rinse with 100 mL ethanol, and blow dry at 40°C to obtain 223.5g3- Methoxy-2,4,5-trifluorobenzoyl ethyl acetate, the yield is 80.9%, and the purity is 98.5%.

Embodiment 2

[0085] Add 220g of 3-methoxy-2,4,5-trifluorobenzoylacetate, 1.1L of methanol and 142.8g of N,N-dimethylformamide dimethyl acetal to a 3L three-necked flask, and react at room temperature for 2h, TLC showed that the reaction was complete and concentrated under reduced pressure to obtain 270 g of ethyl 3-dimethylamine-2-(3-methoxy-2,4,5-trifluorobenzoyl)acrylate. Dissolve 270 g of ethyl 3-dimethylamine-2-(3-methoxy-2,4,5-trifluorobenzoyl) acrylate in 1.35 L of dichloromethane for later use.

Embodiment 3

[0087] Add 54.7g of cyclopropylamine, 1L of dichloromethane to a 5L three-necked flask, and add 3-dimethylamine-2-(3-methoxy-2,4,5-trifluorobenzoyl) acrylic acid dropwise at room temperature The dichloromethane solution of ethyl ester was stirred for 1 h, TLC detected that the reaction was complete, and the reaction was stopped. 2L of water was added to the reaction solution, stirred for 20 minutes, allowed to stand for liquid separation, and the organic phase was washed with 1L of 10% sodium bicarbonate aqueous solution and separated. The aqueous phase was combined, extracted with 1L of dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness to obtain 280.5g of 3-cyclopropylamine-2-(3-methoxy-2,4, 5-Trifluorobenzoyl) ethyl acrylate. 3-Cyclopropylamine-2-(3-methoxy-2,4,5-trifluorobenzoyl) ethyl acrylate was dissolved in 3 L DMSO for use.

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Abstract

The invention discloses a moxifloxacin hydrochloride compound, which is prepared by the steps of: performing Reformatsky reaction on 3-methoxyl-2,4,5-trifluoro benzonitrile to obtain ethyl 3-methoxyl-2,4,5-trifluoro benzoyl acetate, performing enamine formation, amine exchange, nucleophilic substitution, hydrolysis and chelating to obtain (8-methoxyl-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate) boron difluoride, and performing nucleophilic substitution reaction to obtain moxifloxacin hydrochloride. The preparation method of moxifloxacin hydrochloride compound has the benefits that the operation is easy and simple, and the intermediates obtained in each step are high in purity; the reaction is sufficient, the subsidiary reactions are few, and the purification is easy; and the reaction steps are reduced and the industrialized production is easy to realize.

Description

technical field [0001] The invention relates to medicines in the field of medicine, in particular to a moxifloxacin hydrochloride compound with good stability and a preparation method thereof. Background technique [0002] With the widespread use and even abuse of antibacterial agents, bacterial drug resistance is increasing year by year. Drug-resistant bacterial infections not only seriously endanger human health, but also become a thorny problem worldwide. It is reported that about 2 million nosocomial infections occur annually among hospitalized patients in the United States, and about 90,000 of them die. More than 70% of hospital-acquired infections have developed resistance to commonly used antibacterial drugs in clinical practice. Therefore, accelerating research and development can effectively deal with severe infections and drug resistance caused by Gram-positive bacteria, especially methicillin-resistant Staphylococcus aureus (MRSA). Oral antibacterial drugs for no...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
Inventor 严洁王华
Owner TIANJIN HANKANG PHARMA BIOTECH
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